


Whiskey Kisses and a Touch of Lace

by thedropoutandthejunkie (elenajames)



Category: Supernatural
Genre: Aftercare, Comeplay, Crossdressing, Dirty Talk, Drunk Sex, Exhibitionism, Facials, First Time, Light Dom/sub, Light Feminization, Light Incest Kink, M/M, Panty Kink, Rimming, Stockings, Unnegotiated Kink
Language: English
Status: Completed
Published: 2015-02-26
Updated: 2015-02-26
Packaged: 2018-03-15 07:14:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,588
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3438332
Author URL: https://archiveofourown.org/users/elenajames/pseuds/thedropoutandthejunkie
Summary: <blockquote class="userstuff">
              <p>All it takes is one careless moment.</p>
            </blockquote>





	Whiskey Kisses and a Touch of Lace

**Author's Note:**

> My entry for the [Supernatural Kink Big Bang](http://spnkinkbb.tumblr.com/)! (Obviously, I just did a mini-bang but hey). I had the pleasure of being paired with the lovely [femmechester](http://femmechester.tumblr.com/). Art post is [here](http://femmechester.tumblr.com/post/112103458342/whiskey-kisses-and-a-touch-of-lace-ao3-author) and [here](http://femmechester.tumblr.com/post/112255528217/i-illustrated-theboykingsbrokencrowns-fic-for-the)!  
> Huge thank you to my beta [toppysammy!](http://toppysammy.tumblr.com/)

It's taken Dean some time to work up to this. If he'd had his preference, he would've done this in the bunker, where he'd have more privacy, but his gut instinct is telling him it’s a now or never kind of thing. So he waits until Sam is at the library to gather his supplies and locks himself in the motel bathroom.

 

Shaving was a long, painstaking process and he did not escape unscathed. The scattered nicks and slight razor burn on one calf are worth it, though, when the smooth feel of the stockings sliding up his legs sends a shudder down his spine. He runs his fingers over the fabric, tingles spreading across his bare skin as his calluses drag across it.

 

He's dying to linger, to work up to the panties hidden away in his duffle, but Sam is due back soon. Dean slips into his jeans, shoving his feet into his boots. It's thrilling, knowing he'll have the stockings on the whole time they're at the bar, while he's hustling pool and getting them drinks.

 

And yeah, maybe Sam eyes him oddly when Dean's bumped their legs under the table one too many times, just enjoying the feel of smooth satin against rough denim, but he downplays it. He flirts and teases with girls like always, but doesn't quite put in the effort to find one to hook up with for the night. Instead, he stumbles back to the motel with Sam, knocking shoulders good-naturedly and snorting at some stupid ass joke Sam is too drunk to be trying to tell.

 

Dean tries to change quickly while Sam's in the bathroom, but he's only managed to yank off his boots and kick off his pants when he hears a quiet gasp from behind him. Dean's face goes hot, shock and panic dragging him back toward sober. Except suddenly he has six feet of little brother pressed up behind him, trapping him between Sam and the bed.

 

Sam's long fingers are teasing at the tops of the stockings, sending goosebumps racing along the sensitive skin of Dean's thighs.

 

"What's this?" he puffs against Dean's ear, hot and whisky laced, and Dean's knees go weak.

 

"Sam," he whispers, afraid to speak louder, worried that he's dreaming, but Sam just pulls Dean closer, hands still playing along Dean's thighs. Sam huffs a laugh into Dean's neck, and skims his palm lightly over his older brother's hard cock.

 

"This for me, or those pretty stockings of yours?"

 

Dean gasps and trembles a little, there's no way that Sam -

 

"Shh, easy. You're so hot, big brother," he murmurs, pressing kisses down the side of Dean's neck. "So pretty. Is this okay? You want this?" Sam hand shifts away from his cock, both of them coming to rest on Dean's hips, his voice both serious and nervous.

 

"Sam . . . yes, please," Dean rasps, rocking his hips back in Sam’s hold and yes. Sam is hard, and the feel of his cock against Dean's ass sends a thrill up Dean's spine. He can feel the warmth of Sam's breath as he lets out a curse, and his hands tighten on Dean's hips.

 

He pulls Dean around, and Dean thinks for a moment that he's going to be pushed down on the bed until he realizes Sam's real goal: the mirror above the dresser. His face heats at the sight of himself wrapped in his brother's arms, flannel shirt on top and white stockings on the bottom.

 

"I just wanna see. Okay? We can - there's time for more later, I just wanna do this," Sam says quickly, stroking his hands back down to Dean's waistband, pushing down and letting the boxers drop to the floor. Dean steps out of them and kicks them away before being pulled close to Sam's chest. Long fingers pop the buttons on his flannel, then push the tee underneath up, bunching it under his armpits, Sam's arms pinning Dean's to his sides as he wraps around him.

 

Sam runs his hands over Dean's chest, thumbing at his nipples and chuckling at the soft moan it earns him. Dean's cheeks are pink, eyes downcast so he can't see himself in the mirror, and his cock is hard and flushed between his legs. "Look at me, Dean," Sam prompts gently. His hand is tracing small circles over the curve of Dean's belly, teasing just above his cock.

 

Dean swallows and looks up into the mirror. It's easier focusing on Sam's face, on how dark and intent his eyes are than it is to look down at himself or to see the vulnerability he's sure must be on his face. He moans and his hips jerk as Sam's hand wraps around his cock. His brother strokes him slow and firm at first, sucking and nipping marks into Dean's neck.

 

Sam's other hand drops down from Dean's chest to cup and roll his balls and his strokes speed up. Dean can feel his body tensing, toes curling against the carpet, and there are moans and hushed pleas escaping parted lips.

 

"I want to see you come, Dean. Want to see your face, wanna feel you on my hand, taste you," Sam pants hotly over his ear. He thrusts his hips, pressing his cock against Dean's ass. "Want this too, want to see my come leaking out of you, running down to get those pretty stockings of yours filthy-"

 

Dean jerks as the mental image sends him over the edge, his own come spilling down Sam's hand where it's stilled, allowing Dean to thrust into it. His eyes drift shut as he comes, then flutter open, coming to rest on the mirror where he can see the reflection of Sam's hand still on him. His brother's fist is streaked with white and he can feel it running down his shaft to his balls. Slowly, Sam withdraws and holds his hand in front of Dean's mouth. Dean takes the hint, lapping with his tongue to clean Sam's hand, feeling tired and oddly content. He brings up one hand, gripping Sam's wrist to draw it closer and sucks sticky fingers into his mouth.

 

"Fuck, Dean," Sam groans and shit. Sam's still hard, pressed up against Dean’s ass, and Dean lets lust override any qualms his mind might have. He turns and drops to his knees, letting the moan that's dragged out of Sam's mouth wash over him. Closing his eyes, he nudges his brother's hard cock. Even through denim, Dean can feel the heat and he whimpers, pushing his face against Sam's thigh before looking up at him.

 

Sam's face is flushed, lips bitten pink, and eyes wide as he looks down at Dean on his knees. He runs knuckles over Dean's stubbled cheek, and concern washes over his expression.

 

"Dean, are you sure? I don't . . . I don't expect anything, okay?"

 

"I want to, Sammy. Want to taste you, too. Please?"

 

"Yeah, Dean. God, go ahead," Sam breathes.

 

Dean pops the button on Sam's jeans and draws the zipper down, pulling the denim and boxers down far enough that they drop, and Sam kicks them away when they hit the floor.  His brother’s cock is long and curves upward slightly, lightly veined and dusky. Dean traces his tongue along its length, using one hand to hold it steady as he sucks lightly on the head. Sam twitches and lets out a groan, eyes focused over Dean on the mirror when Dean looks up. He shudders at the mental image of what Sam has to be seeing in the mirror. Sam shifts his gaze back down, threading his fingers through Dean’s hair. He doesn’t push or tug, but Dean slides his mouth down around him anyway, sucking a little as he starts to bob is his head.

 

Sam’s big enough that Dean needs his hand to stroke what he can’t take, and he has to work to set up a rhythm with his mouth and hand. He keeps his eyes on Sam’s face as much as he can, feeling a thrill at the shocked, pleasured expression there, the way Sam’s mouth is open just a little and the pink of his cheeks.

 

Carefully, Dean draws his other hand up to cup Sam’s balls, rolling them slightly and slipping a finger behind them to stroke over the skin there. Sam jerks into his mouth, making Dean’s eyes water but its worth the choked moan he gets in return. Soft curses and praise reach him, then suddenly Sam is pulling out, cock still barely in Dean’s grip when he comes, splashing over Dean’s face and thrusting into his hand. Dean quickly shuts his eyes, only opening them when he’s sure none of it is going to land in them.

 

Sam thumbs over a streak of come on Dean’s cheek and presses it to his lips, groaning again when Dean sucks it in and licks it clean. Sam moves away to snatch up his discarded shirt, carefully cleaning Dean’s face before pulling him up and into a kiss. “Thank you,” he breathes against his lips.

 

Embarrassment is making itself known again, sending Dean’s stomach sinking and his face burns hot. He looks down, away from Sam’s gaze only to clench his eyes shut when he sees his own stockinged feet.

 

“Hey,” Sam says softly, stroking his cheek and drawing his chin up for another kiss. “You okay? Was that alright?”

 

“You can’t want this,” Dean says quickly. “This is so far from normal, Sam, so far from okay. There’s no way you could like this.”

 

“Well, it’s a good thing for you and I both that you don’t get to decide what I like. And I like this very much, Dean. I’d like more of it, if you do.”

 

Damnit, how can Sam’s voice be so sure, so fucking calm? An hour ago he didn’t have any idea that Dean was wearing stockings under his boots and now he’s proposing - what, that they become fuck buddies?

 

“You regret it already, huh,” Sam’s tone is wry, and he’s starting to pull away. Dean finds himself tipping his face to keep contact with Sam’s hand, halting his brother’s retreat.

 

“I don’t know what this is, Sammy,” he says quietly. “I never thought about this. Ever.”

 

Sam huffs a laugh, cheeks dimpling and something in Dean unclenches. “And I have?” His lips brush over Dean’s, more a caress than a kiss. “Let’s get you cleaned up, hmm?”

 

Sam guides him to the bathroom, starting the shower and watching with heated eyes as Dean strips out of his shirts and carefully rolls the stockings down his legs. It’s cramped in the motel shower, forcing them close together as they take their turns under the spray. Sam carefully massages soap through Dean’s hair, washing away sweat and come, and it almost feels like a trust fall when Dean allows his little brother to tip his head back under the showerhead to rinse the soap away. Scratchy towels are buffed over wet skin, but they’re big enough guys that they always come out damp.

 

Dean falters when they leave the bathroom, but Sam strides right over to his duffel to pull on boxers and sweats, so Dean follows suit. Sam is folding the covers back when Dean turns around, yanking free the tucked in corners that often trap his too-long legs. He sits on the edge of the bed, meeting Dean’s eyes where he’s frozen on the opposite side of the room. After a moment, Sam clears his throat.

 

“Do you want to um . . . “ he trails off quickly, but Dean knows what he’s asking. Giving a silent nod, Dean skirts around the ends of the beds to sit on the other side of Sam’s. They shuffle awkwardly as they lay down, and Sam reaches up to twist at the knob on the light until it clicks off, casting the room into shadow. It’s silent in the room, almost uncomfortably so because it feels like they’re both holding their breath.

 

“So. This is awkward,” Dean finally deadpans and Sam laughs. He grabs Dean’s arm and tugs him closer, so that Dean is curled up along Sam’s side, head on his shoulder. Dean is dubious about his ability to sleep like this, but his breathing syncs up and slows down in time with Sam’s so that neither can be sure who drifts off first.

 

Morning the next day isn’t nearly as awkward. Both brothers wake up in desperate need to use the bathroom, and Sam grumps at Dean from the doorway while he waits. Dean dresses while Sam’s brushing his teeth, and they’re out the door well before checkout time. There’s a diner down the road, and their stomachs are growling by the time they’re settled in a booth. Dean scans over the breakfast crowd while Sam flicks through a couple of newspapers, looking for any sign of a case. Honestly, Dean’s not too concerned about finding another job right away. His mind is preoccupied with what happened between his brother and himself (and he’d be a liar if he denied that his body wanted to be preoccupied, too).

 

“Did you mean it?” he finally asks when the waitress has left with their order, knowing they’ve got a while before she returns.

 

“Did I mean what?” Sam asks, tone puzzled.

 

“What you said about getting my stockings dirty,” Dean says low. “What you said about not having expectations, cause man, I - It sounds like you want things, anyway, and I’d kinda like to know more about that.” He’s rambling a little, trying to avoid flat out saying ‘hey, did you mean it when you said you wanted to fuck me’ in a diner full of old folks and families.

 

Sam lets the paper flop down enough that he can see Dean over it, eyes flicking over his brother in a way that makes Dean’s cheeks heat. “I meant what I said, Dean. I don’t want you to feel like I expect things because of what happened, but I would like more. I want more, but I’m not going to push you into anything you don’t want.”

 

It’s an odd relief to hear it plainly like that, matter-of-factly stated over a paper and coffee in broad daylight, not heady words spilled out during sex. Dean relaxes a little and nods. “We’ll talk, later? About. . . more. That work for you?”

 

Sam smiles and nods, flicking his paper back up when it’s obvious that Dean is done with the conversation for now, especially when the waitress returns with their food. Their conversation is pretty standard, Sam pointing out an odd string of murders reported a few towns over, and they decide to check it out since they’re close by. Dean proclaims the diner food awesome, leaving a healthy tip for the waitress in cash rather than putting it on the card as he gets up to pay. Sam folds up the papers and follows Dean out, pulling out his phone to do some more digging while they’re on the road.

 

Two interviews later that day, and the job has already turned out to be a bust. Another witness had gone in to the police, giving them the description of the very human guy she’d seen breaking into the most recent victim’s home. They have the motel for one more night at least, so they head back there to change out of their suits.

 

Sam goes out for food and beer while Dean opts for a nap, pulling the blinds shut tight and flicking off the lights. They’ve been running hard, with little downtime in between jobs. He’s not sure how much time has passed when he hears the click of the door. He can tell Sam is trying to be quiet, even though his brother has to know that Dean’s awake anyway. Beer in the fridge, food on the table, and Sam shuts the bathroom door before flicking on the light. With a sigh, Dean rolls himself over and stretches lazily, letting his eyes drift shut. He’s comfortable after the nap and not quite ready to get up, despite the lure of food and beer. Light shines behind his eyelids when Sam opens the bathroom door, vanishing with a click.

 

“Want a beer?” Sam asks.

 

“Sure,” Dean yawns, finally dragging himself up to push the curtains open. It’s a whole two hours later, he realizes in shock when he glances at his watch. “Where you been, Sammy?”

 

“Did a little shopping is all. Eat, man, before the food gets cold.” Sam is avoiding, and that’s fine with Dean for right now. He’s not awake enough for deep conversations, and his stomach is growling. Sam pushes Dean’s beer over to the other side of the table and started opening takeout boxes, so Dean settles in and nabs a carton of orange chicken. The stuff is good, Sam’s bizarre knack for picking good take-out places paying off once more, and Dean’s feeling good after food and a nap.

 

“What kinda shopping did you do, then?” he asks, figuring now is a good of a time as any. Sam looks a little startled that Dean brought it up, and Dean can’t decide if he’s more pleased or nervous about the blush that rises in his little brother’s cheeks.

 

“I’d like to . . . try something. Only if you’re open to it, if you think you’d like it. If not, I kept all the receipts so we can return the stuff I got,” Sam says slowly, getting up to grab the bags off the bed and holding them out to Dean.

 

Dean meets Sam halfway, taking the bags and setting one on his own bed before pulling out garment after garment. Each piece gets laid out on the bed, and as Dean surveys it, he’s not sure what to feel. There are a couple of skirts, women’s cut shirts, stockings, panties, and bras. Everything looks like it will fit, although some of it a little snugly. Which, in all honesty, might just be what Sam was going for.

 

“Dean?” Sam says softly.

 

“Why?” Dean says in response, looking up to study Sam’s face. Sam’s gaze darts to the items on the bed, skims over Dean’s body, and returns to meet his. Fuck. That look is hot, and Dean is getting hard already. “You really mean it, don’t you. Want to dress your big brother up all pretty, then make a mess out of me, Sammy?”

 

Sam pushes forward in an instant, and their kiss is earnest, desperate. It’s Sam that pulls back, separating them completely and holding Dean at arm’s length when he tries for more. Dean tries to shutter the hurt look he knows dances across his expression, but Sam catches it. Warm fingers trace over his lips and cheek, gentle and reassuring.

 

“I do, Dean. I really do, if you want to. I wanna, right now, but -”

 

“But more talking, yeah?” Dean says with a wry smile.

 

“I just don’t want to cross any lines, here, Dean. I mean, we already kinda took a big leap without really saying anything about it, and I don’t want that to come back to bite us.”

 

Yeah. Incest is a pretty big fuckin’ leap, alright, Dean supposes. “You know that’s not the first time I thought about it. About you, like that,” he admits, deciding to go for broke. “But you were my little brother, so I told myself you were off-limits.”

 

Sam looks a little stunned at his admission, and Dean wonders if he’s said too much when Sam clears his throat. “Is it weird that I’m glad I’m not the only one?,” he tries for a laugh, and Dean grins at the little brother awkwardness of it. Sam takes a few steps back to sit on the bed, and Dean follows as Sam keeps talking. “I thought maybe it was just a thing. Too much time together, too many stories about your sexcapades. I chalked it up to hormones and misguided fantasies.”

 

“So what got you to the point of jerking your brother off in front of a mirror? Not that I’m complaining,” Dean rushes to explain when Sam starts looking worried. “Just not what I expected to happen when you saw my, um, stockings.”

 

“Other than too much Jack?” Sam shakes his head. “I don’t know. Some part of me just wanted to try. Worst case, you punch me in the face and maybe never talk to me again. Or blame it on the liquor and never let me drink again. But you got hard the moment I touched you and I could see it. I just had to make sure I wasn’t taking advantage. I still have to.”

 

“Advantage of what?” Dean’s a little incredulous. Sam knows he can hold his own in any fight, including against Sam.

 

“You’d give me anything, Dean. You always have,” Sam’s voice has gone soft again and he reaches to thread their fingers together on the bedspread. “I couldn’t take it from you if it wasn’t good for you, too. That’s why we gotta talk about it, make sure we both want it. We need safewords, and limits, and to talk about what else we might want to try, or even if we want to keep doing this.”

 

“I want it. I want you, Sam, and I want to try this with you,” Dean murmurs, scooting closer to Sam on the bed. “So we’ll figure it out, set down some rules and see what happens, hm?” He presses a kiss to Sam’s forehead when he nods.

 

They agree that tonight is too soon, so Dean packs away the clothes Sam bought for him, and they stretch out together to watch a movie. Bright sunlight drags Dean out of sleep, and he can’t help but grin when he sees Sam is curled up by his side. They’re gonna need to get a bigger bed from now on, he realizes as he tries to sit up and nearly falls off the side. The thought leaves him with an odd warmth in his chest. He scurries into the shower before he can think too much of it.

 

 

* * *

 

 

A few hunts and a couple states later, they both think they’re ready. They each took the time to write out their kinks, interests, and hard limits. Dean’s surprised to see how similar his lists are to Sam’s the first time they share them with each other. Road time and downtime now consist of discussions about their kinks, experiences good and bad, and a few whispered conversations about hell and torture.

 

Motel rooms are now king sized beds when they can get them, squashing into a single queen when they can’t,  and shared showers when the shower space allows. There’s cuddling and kissing and the two of them are sleeping better than they have in years. Sex has been limited to handjobs, blowjobs, and what Dean has learned is called “frottage.” Turns out Sam is as talented with is mouth as he is with his hands, and Dean loves the wrecked look on his little brother’s face when he comes in Dean’s mouth. He wonders what Sam will look like coming in Dean’s ass.

 

There’s a spark of anticipation the air when they check in to a hotel for the night, spending a little more than they normally would for a nicer place. Dean knows its worth it when he gets in the shower. The water is hot and the pressure is awesome, loosening the knots in his back and the ache of stiff joints from riding in the car. He doesn’t really feel rushed to save water for Sam, knowing that the water heater here can probably take it.

 

Sam hops in while Dean towels off - even if the bathroom’s nicer, the shower space isn’t big enough for them both - and he only slips on a pair of boxers before getting into bed. The bed itself is comfortable, and Dean indulges in snuggling down between clean sheets while he waits. His heart rate kicks up a little when the shower shuts off, and he feels a bit silly. This is Sam, he reminds himself firmly. Dean can see his brother’s shadow in the moment before the bathroom light clicks off, and Sam rounds the bed to settle in on the other side. Silence reigns for a moment before Sam gives a little snort.

 

“Come here,” he says softly, scooting closer to Dean and pulling the other man to his side. They lay quietly together, relaxing into each other’s warmth. Dean sighs contentedly when Sam starts stroking over his back and hip in slow circles. It’s unexpectedly tender, and Dean’s not sure what that means for them, but damn if he doesn’t like it. He pushes himself up on one elbow, leaning over for a kiss. Sam smiles, and Dean can feel the quirk of lips against his own.

 

Dean lets Sam tug him up and over so that Dean is straddling Sam’s hips and Sam’s hands come to rest on Dean’s waist. Sam follows Deans lead, keeping their make out slow and easy. Fingers roam over soft skin and familiar scars, caressing and heating their kisses up. Sam is nippier than Dean expected, and an experimental bite to his little brother’s bottom lip earns him a quick jerk of hips that brushes them together. They moan into each other’s mouths, and Sam’s hands settle on Dean’s ass, sending a shivery thrill up Dean’s spine when he strokes a thumb under the waistband of Dean’s boxers.

 

Dean shifts off of Sam long enough to strip his boxers as Sam does the same beside him. The close contact between them when Dean straddles Sam again makes them both groan, and their next kiss is more heated. Sam urges Dean closer, moving his hips so their cocks brush along each other, and the friction is more maddening than it is pleasurable.

 

“Sam,” Dean grunts, rutting against his brother. In a tangle of limbs, Sam rolls them over, and Dean can’t help but enjoy the spark of pleasure Sam’s manhandling causes. One hand slips just under Dean’s hips, tilting them up toward Sam, and changing the way they grind together. It’s good, much better like this, and Dean rolls up into every rocking motion. Their movements are almost frantic, and Sam huffs a laugh against Dean’s neck.

 

“What the fuck are you laughing at?” Dean huffs, slowing down his movements.

 

Sam leans up and grins down at his brother, pace brought back down to those teasing brushes again as he lets Dean back down to rest on the mattress.

 

“Feel like a couple of teenagers dry humping to get off,” Sam explains breathlessly, trailing the fingers of one hand down Dean’s chest.

 

Dean sighs and flings his arm over his eyes. “You are such a buzzkill, Sammy.”

 

“Aw, baby, now don’t be like that.”

 

Snorting lightly at the cheesy line, Dean tries to get himself back on track. He’s caught off guard when warm air puffs briefly over one nipple before it’s taken between teeth and tugged gently. Dean curses, the pleasurable pain causing him to arch toward Sam’s mouth. Sam nips the other side the same way, laps at them soothingly, and starts to kiss and nip his way down Dean’s torso. Of course, Dean catches on to Sam’s endgame quickly and readily spreads his legs to make room for his brother’s broad shoulders.

 

Dean looks down just in time for Sam to look up, catching his eye and the sight of Sam’s dirty grin just inches above his own hard cock is a sight Dean knows he’s never going to forget. Sam laps at the head, the short track from frenulum to tip so sensitive it almost hurts. Just when Dean is about to beg for reprieve, Sam licks his way down Dean’s cock and sucks lightly at his balls. A juddery sigh and fingers brushed through Sam’s hair tell Sam how much Dean likes the attention, and that grip tightening when he flicks his tongue over Dean’s perineum makes him smirk. Sam presses a little harder, relishing in the jerk of his brother’s hips and the shocked gasp from above him.

 

“Sam? Sam what - ah!”

 

Sam’s forced to grip the back of Dean’s thighs tightly to keep his legs apart as he rims him slowly. This was on both their lists, a solid green and Sam’s been dying to see how Dean reacts; he certainly isn’t disappointed. He’d smile if he could, but he just pushes deeper, dedicating himself to pulling every gasp and moan from Dean that he possibly can. Sam feels the moment Dean just lets himself enjoy it; his body relaxes, sinking down into the bed, and Sam’s tongue finds it easy to tease itself inside Dean. Of course, that’s when Dean tightens at the sensation, forcing Sam back out, so Sam sits back up.

 

Dean is pink-cheeked, mouth slightly open and his gaze is slightly stunned when he looks up at Sam. He’s irresistible. Sam swipes a hand over his mouth before leaning down for a kiss, and he ends up having to brace himself over Dean when strong hands yank him down to met his brother’s mouth.

 

“Jesus, Sammy,” Dean pants against his lips.

 

“You want more?” Sam breathes back. He watches as Dean’s eyes close for a moment, the embarrassment that flickers over his face before he’s back to looking at Sam and nodding shyly. Sam brushes another kiss over Dean’s lips.

 

There’s lube on the bedside that he’d left out while Dean was in the shower. It’s a fresh bottle of stuff recommended for anal - Dean hated that word, but had stuck by Sam in doing the research - and Sam appreciates the feel of it as he warms some on his fingers. It’s thicker than what he’s used to, meant to last longer so they’ll have to reapply less often, and, most importantly, there’s less chance of him hurting Dean.

 

It’s tight and hot as he pushes one finger slowly into Dean. Sam only gets up to one knuckle, then starts thrusting shallowly. He can feel the flutter of muscle around his finger as Dean tries to make himself relax.

 

“You okay?” Sam asks softly, noting the uncertain look on his brother’s face.

 

“Just feels weird. Knew it would at first, I guess, but  . . . just hurry up, would ya?” Dean grumbles the last part a little.

 

To keep him distracted, Sam takes Dean’s hand and pushes it toward his own cock. There’s a sigh and the muscle around Sam’s finger loosens as Dean strokes himself slowly. Good. Sam wants to do this right, regardless of Dean’s impatience as Sam stretches him open. He stops to add more lube a couple of times, and it makes the glide of his fingers in and out of Dean’s body smooth and easy.

 

“Sam,” Dean finally urges quietly, and Sam nods. He takes the offered condom and rolls it on, adding a little extra lube to cover the tacky feel of the thin layer already on it.

 

Dean’s legs are pulled up to rest on Sam’s shoulders, and Sam quietly appreciates the angle it gives his brother’s ass. He presses his cock just against Dean’s hole, stroking his thigh soothingly as he starts to push in. The slide is tortuously slow, and Sam puts all of his focus on Dean’s face. Discomfort is there, sure, and a slight twinge of pain that has Dean sinking his teeth into his bottom lip. He moans when Sam’s hips meet his ass, though, and Sam can’t help but kiss him.

 

“Are you alright?” Sam murmurs.

 

“Doesn’t hurt,” Dean reassures him, knowing that’s what Sam’s asking. “Move? It feels like - like maybe it could-” Sam thrusts slowly, rolling his hips to keep his movements smooth. “Good. Yeah, good Sammy, please.”

 

Their pace builds gradually, until Dean’s using what leverage he has to rock up into Sam, and Sam brings one hand down to stroke his brother’s cock. He doesn’t want to get there before Dean, not when it’s his first time bottoming, and that idea is coupled with a desperate need to see what his brother looks like under him like this when he comes.

 

Dean pulls him down for a kiss and soft little sounds fill Sam’s mouth. Begging, Sam realizes. Dean is pleading quietly, using Sam’s mouth to muffle the sound. It tugs at something in Sam, something protective and fierce, and it fans the flames of his need to satisfy.

 

“I got you, Dean,” Sam breaks the kiss to whisper, voice loud in the otherwise quiet room. “You’re so close, baby, I want you to come. Want to see you like this, know that I’m making you feel good.” He speeds his thrusts, adding a careful sweep of fingers over the tip of Dean’s cock on every upstroke  of his hand, and that does it. Dean’s legs tighten up, and he tosses his head back, voice hoarse as he gives a sharp cry. Sam strokes him through it, drinking in Dean’s every reaction.

 

He’s ready to pull out and jack himself off when Dean wraps his legs around Sam’s waist. Firm fingers tug Sam’s hand away from Dean’s cock, and Sam groans when Dean starts licking his hand clean. Dean stares up at him through hooded eyes, and he keeps moving to meet Sam’s thrusts. Sam can feel the clench in his gut just before his orgasm hits, and Dean chooses that moment to suck Sam’s fingers into his mouth.

 

“Oh, fuck,” Sam whimpers, his voice cracking, and he buries his face against Dean’s throat.

 

“Sammy?” Dean murmurs after a moment. Sam sighs and pulls out carefully, getting rid of the condom and tossing the lube back on the nightstand.

 

“Was that alright?” Sam asks, stretching out beside his brother.

 

Dean just snorts. “I came on your cock and licked my jizz off your fingers, and you’re wondering if it was alright?” He’s quiet for a moment, and sighs. “It was perfect, Sammy. Thank you.” Suddenly, Sam has an armful of big brother pushing into his space, snuggling into his embrace. “Now, cuddle me.” Sam can only do as he’s told with a laugh, holding Dean close.

 

 

* * *

 

 

Sex with Dean is awesome. And time consuming, as it turns out. Sam certainly knew his brother had a high sex drive, but knowing about it and being expected to keep up with it are two different things. They move from fucking only in the bed at night to the shower in the mornings, from over rickety motel tables when they check in to over the Impala’s hood after hunts. Slow and sweet, adrenaline-fueled and rough, Sam soon finds himself hungry for it just as often as Dean is.

 

Sometimes, though, there’s a sense of tension and waiting, and Sam knows it’s that line they crossed the first time that they haven’t looked at since. He’s still not sure where Dean keeps his stockings and panties, or if he should even bring it up before Dean does. The bags of clothes Sam had picked up are surprisingly conspicuous in the space they occupy in the trunk, and he debates bringing them in at every stop they make. A part of him wants and remembers how willing Dean was to give that night, but he’s not willing to cross any lines.

 

Dean makes the decision for him, bringing in the bags from the trunk without a word and tossing them on the bed before heading into a shower. Sam heads out for beer and pizza like always, although its hard to focus on hunger when he has images of his brother in a skirt running through his mind. He kills some time waiting for the pizza on his phone looking up clubs and bars nearby, and sure enough there’s one that looks promising, and he hopes like hell Dean will be up for playing out this particular fantasy.

 

Dean is lounging in boxers when he gets back, hair in damp, soft spikes, legs noticeably smooth, and quietly flicking through TV channels. He offers the remote to Sam once Sam has settled on the bed next to him with the pizza and beer between. Sam finds a romcom and leaves it at that, cracking open a beer and digging into the pizza. He’s not surprised when Dean finishes first, grabbing the bags from the other bed on his way back to the bathroom.

 

Wiping his fingers clean, Sam gets up to dig through his bag for his tightest jeans and a black tee. Simple, sure, but he wants the attention to be on Dean tonight; Sam gets enough attention for his height anyway. He fights the urge pace, sitting patiently on the edge of the bed. Faint sounds of shuffling and a couple of curses come from the bathroom, and Sam can’t help but smile.

 

Just when he starts contemplating offering Dean help - or an out - the doorknob rattles and the door cracks open just a little.

 

“You better be sure about this Sam. You better be goddamn sure about this cause if you laugh-” Dean says, trying to sound grumpy but only sounding nervous.

 

“Dean. I picked out those clothes for you. I’m not going to laugh.”

 

Then Dean is in front of him, cheeks a little pink, and his hands desperately trying to shield the sight of his hard cock beneath the fabric of his skirt. Sam knows he’s gaping and he knows he should say something, but all he can do is drag his gaze over Dean’s body.

 

“Yeah, definitely not laughing,” he finally manages, and God, does Dean look shy? Sam stands and pulls his brother into his arms. Dean clings to his shirt and Sam can feel him trembling. “Are you okay?”

 

“I’m . . . I’m not sure if I’m more nervous or turned on,” Dean admits, voice slightly muffled by Sam’s shoulder.

 

“You don’t have to be nervous, Dean. You look - God, you’re gorgeous,” Sam murmurs, stroking his hands over Dean’s back.

 

“Sap,” Dean teases, but it comes out more like relief. “But why are you all dressed up?”

 

“I was thinking about going out,” Sam says softly. “There’s a bar nearby I thought we could try, if you feel comfortable enough to.”

 

Dean stays tense and silent in Sam’s arms for a long moment. Sam’s sure he’s overstepped and asked Dean for too much too soon.

 

“Is it safe?”

 

The question is startling, vulnerable in a way Sam wasn’t prepared for. He shifts back enough to look at Dean’s face, only to find that Dean’s gaze has dropped to the floor. It makes him ache, and he’s not sure if he wants to wrap Dean up in his arms away from the world or find out and tear apart who or whatever caused his brother this kind of fear.

 

“It’s an LGBT friendly bar, Dean. I don’t think anyone will bother us, and it’s not like we can’t hold our own if anyone does. If you’re not okay with it, though, we don’t have to go.”

 

“No, let’s go,” Dean decides.

 

Dean’s a little unsure in the boots he’s wearing, the slight heel enough to make him wobbly on the walk to the Impala. It isn’t far from motel to bar, and they chat normally enough through the drive that Sam can see Dean relax. He slips an arm around his brother’s waist once they reach the bar, hand teasing at the strip of bare skin not covered by the blouse and skirt Dean has on.

 

Friday night means the bar is pretty busy, the darker lighting and loud music giving it more of a club vibe, especially when Sam makes note of the crowded dancefloor. There isn’t much for seating, but Dean drags him toward a tiny high top once Sam’s managed to snag them a couple of beers from the bar. He pushes Sam onto the tall stool, and Sam sits with legs spread so Dean can settle between them. Dean leans back against Sam’s chest, beer in hand as they both watch the people out on the dancefloor.

 

They drink their beers, content to just observe for now, and it’s nice to have Dean this close in public. Some people are looking right back, calculating and flirty glances alike, and a dirty thrill runs through Sam when he notices another guy in particular giving Dean a very thorough once over. His gaze jerks away when he realizes Sam has caught him staring, but every now and again he glances back their direction.

 

“You have an admirer,” Sam leans forward to speak into Dean’s ear, slipping his arm around Dean’s chest. “Three o’clock.”

 

Dean shifts to look and Sam can feel the short laugh he gives. The guy looks a little awkward under their attention, both of them blatantly looking at him now. He seems to come to some kind of decision, pushing away from the wall to approach them. Leaning close, he has to shout to be heard above the music.

 

“Do you two want to dance?”

 

Sam’s oddly pleased that the guy has (correctly) assumed that they come as a set, and he nods without thinking. He pushes a little at Dean’s back to get him to step forward, giving Sam room to slide off the stool. Stanford is a long time off, but Sam remembers enough of how this works to set up a rhythm once they’re out on the floor. Dean’s turned to face him, sandwiched between the two men. The stranger has one hand resting on Dean’s hip, just above Sam’s while the other holds his drink. He presses Dean against Sam and the three of them settle into a dirty grind.

 

Two songs in, Dean tugs Sam down to so he can talk to him. “He’s hard,” he says roughly, and fuck that definitely shouldn’t make Sam’s own cock twitch.

 

“Yeah?” Sam growls back, his eyes meeting the dark gaze of the stranger. “You like that? Knowing you’ve got us both so turned on, Dean. That some guy who doesn’t even know your name is hot for you when you’re all dressed up?”

 

Dean groans, and impulse has Sam stepping back, spinning Dean to face the other man before pressing them back together. Sam slides his hands under Dean’s skirts, thrilling at the ruffled fabric of his panties, and he can feel when the stranger’s hands come to rest on Dean’s waist above the fabric. Dean runs his hands up the other man’s arms, arms draping lightly over his shoulders as they dance. This position makes it easy for Sam to press his cock against Dean’s ass, and he can’t help but mutter into Dean’s ear.

 

“You feel that Dean? Can you feel him?”

 

A roll of Sam’s hips sends Dean’s panty-clothed cock skidding along the rough fabric of the stranger’s jeans. He laughs a little when the guy’s eyes go wide at Dean’s moan and immediately does it again. Soon, the guy is using his hands to guide Dean’s hips until Dean is practically humping his thigh, ass rocking back into Sam’s cock.

 

“Sammy,” comes out high and strangled, and Sam reaches out to still the other man’s movements. The guy looks up curiously, gives a quick nod to show he understands, and eases back.

 

“You okay?” Sam asks.

 

“Yeah. Just...got close,” Dean answers, and Sam is sure he’s blushing. Sam groans, nuzzling Dean’s neck.

 

“Dirty boy,” he says softly, gratified when Dean shivers. “Almost coming, grinding on a stranger in a bar? But you didn’t. No, you were good for me, weren’t you?”

 

Dean grinds back against Sam and nods, sinking into Sam’s hold. The stranger graciously takes it as his cue to leave, nodding at Sam in thanks, and stumbling off toward the bar, presumably for another drink. Sam watches him go, contemplating. A threesome is an intriguing thought for another time. Maybe. There’s a tendril of possessiveness and jealousy curling through Sam, coiled up with lust at the idea of someone else touching Dean.

 

Sam leads his brother off the dancefloor, back toward the still-empty table. He ignores the chair in favor of crowding Dean up against the wall. The kiss is desperate at first before shifting into something slow, hot, and heady.

 

“You ready to go?” he breaks the kiss to ask.

 

“Yeah, Sammy,” Dean says breathlessly. Sam leads them through the club and out the door, rushing to where they’d left the Impala. Impatience makes Dean speed back to the hotel, and he barely remembers to lock the car.

 

Sam has him pinned to the back of the door in an instant, fingers finding the lacy tops of Dean’s stockings and brushing teasingly over fabric and soft skin until he’s gripping the backs of his thighs. It makes it easy to rub them together, a mimicry of what happened at the bar, and Sam admires how quickly Dean’s cheeks blush.

 

“You were close huh? Close to coming all over that guy. And you know, all I could think about, Dean, was what it would look like if he made you come; when he realized that you’d gotten those pretty panties of yours dirty. Do you think he would’ve come, too?”

 

“Jesus,” Dean moans, “Christ, Sam, what-”

 

Sam cuts him off with a kiss. “I want to fuck you so bad, Dean.”

 

Dean laughs then, pushing Sam back and practically sashaying over to the bed. He kicks off the boots before settling on the bedspread on his hands and knees, sending a dirty look over his shoulder at a gobsmacked Sam.

 

“C’mon little brother. Thought you wanted to fuck me,” Dean rasps, pushing his ass out so just a hint of cheek peeks out from under the edge of the skirt.

 

Sam strips off his shirt on the way to the bed, tugging his belt loose, but leaving his jeans on. He flips Dean’s skirt up and curses in surprise. These are definitely not any of the panties he’d picked up. These are split starting at the top of Dean’s ass, and the opening runs down between his thighs. There’s a line of fabric that starts just below Dean’s balls, telling Sam the front isn’t as open as the back but the idea of Dean wearing these all night . . .

 

“Been saving these,” Dean says softly, craning his neck to look at Sam.

 

Wordlessly, Sam thumbs along the twin hems of fabric framing Dean’s hole, spreading the cheeks apart. He can’t help but lean forward, flicking his tongue over the sensitive skin. It’s a tease rather than a real lick, and he smirks when Dean pushes back.

 

“Fucker,” Dean gasps, dropping his forehead to the mattress.

 

Sam presses back in and hums in agreement, earning himself another curse. His brother gives in to a good rimming more easily than Sam ever would have dreamed, and he loves making Dean fall apart on his tongue. Every lap edges nearer and nearer to Dean’s sac, and Sam pushes gently at his perineum, earning a faint plea.

 

“What was that?” Sam questions as he pulls back.

 

“Please. Please, Sam.”

 

“Tell me what you want.”

 

“Fuck me, Sammy, please.”

 

“Good, Dean,” Sam pants, unzipping his fly and freeing his cock. He slips a small packet of lube out of his pocket, carefully tearing it open and spreading it on his fingers. One slides easily into Dean, and he slowly works a second in beside it, fingering his brother for as long as he knows he can get away with before Dean loses patience. Squeezing out the last of the lube, Sam strokes it over his cock and lines up.

 

“Do it, Dean,” Sam says low.

 

Dean pushes himself up on his hands again, arching and pushing back. They grunt in tandem when the head of Sam’s cock breaches Dean’s hole. Sam struggles to hold still while Dean takes him inch by inch and he shudders when the fabric of Dean’s panties finally brushes the bare skin of his belly. Dean manages a couple of slow, frustrating thrusts before Sam grips his hips and drags him back onto his cock.

 

Sam sets a rapid pace, and Dean anchors himself as best he can in the bedding, pushing himself back into every thrust. His head hangs low between his shoulders, and, on a whim, Sam reaches out with one hand to grasp Dean’s hair. He yanks his brother’s head back, angling it to the side so when Sam leans forward he can sink his teeth into Dean’s neck. Dean tightens around him, bucking in his hold as a cry tears from his throat.

 

“Touch yourself, Dean, want you to come in those pretty panties of yours,” Sam growls against the tender, bitten skin. He can tell the moment Dean’s hand begins stroking his cock; Dean slips a little on the bedding, changing the angle of Sam’s thrusts, and suddenly his brother is much tighter around his cock. “God yes,” Sam hisses, and he slides the hand on Dean’s hip around to cup Dean’s balls, Dean’s hand bumping his own on every downstroke.

 

“Fuck, fuckfuckfuck, Sam!” Dean cries, and Sam can feel the way his balls draw up to his body. He slips a finger behind to press at the tender flesh there and Dean practically writhes on his cock. Sam comes with an erratic thrust of hips, pressing his face into Dean’s back.

 

The room is quiet save for the sound of their breathing. Sam knows he needs to move soon, that the way Dean’s back is curved can’t be comfortable anymore, but his limbs feel like lead. With a sigh, he pushes himself up. He’s about to pull out when a thought strikes him, and he sneaks one hand into his pocket.

 

Sure enough, a slow trickle of come slips down Dean’s thigh when Sam’s cock slides out. Sam grips Dean’s hip with one hand to keep him from flopping down on the bed the way Sam knows he wants to, causing Dean to glance back curiously.

 

“What- Sam, what the fuck?” Dean demands, trying to pull away.

 

“Shh, baby,” Sam mutters. “Push out for me, please?”

 

Dean mumbles something about Sam being a kinky bastard but does as he’s asked, pushing his ass out and bearing down. Hot come slips out of him and he can feel it drip down his balls and thighs. Eventually, Sam pats his thigh and Dean slumps down on the bed, rolling over to glare at his brother. Sam looks smug as he hands the phone over without a word, and Dean can’t help but gulp as he hits play.

 

It’s different - and hot - being able to see from this angle. His ass is pink and stretched, and there’s a glisten of lube and come on the tender skin. He watches himself as he pushes out, and groans as the camera follows the trails of come down his legs to where they soak into the fabric of the stockings.

 

“Oh, you are so saving that,” he says, handing the phone back to Sam.

 

“That was the plan,” Sam grins, laying down beside him heedless of the come on the bedspread. Dean rolls to press against his side, sighing contentedly when Sam wraps an arm around him.

 

“It’s still early you know,” Dean says offhandedly.

 

“Oh I know. Give me a little bit, then I’m going to see what else you have under that skirt of yours.”

 

“Deal.”

 

 


End file.
